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Highly diastereoselective 1,3-dipolar cycloaddition of nonstabilized azomethine ylides to 3-nitro-2-trihalomethyl-2H-chromenes: synthesis of 1-benzopyrano[3,4-c]pyrrolidines

Authors :
Vladislav Yu. Korotaev
Mikhail I. Kodess
Evgeniya G. Matochkina
Vyacheslav Ya. Sosnovskikh
Alexey Yu. Barkov
Vladimir S. Moshkin
Source :
Tetrahedron
Publication Year :
2013
Publisher :
Elsevier BV, 2013.

Abstract

Reactions of 3-nitro-2-trifluoro(trichloro)methyl-2H-chromenes, including 2-unsubstituted derivatives, with N-alkyl-α-amino acids (sarcosine, proline) and paraformaldehyde proceed diastereoselectively to give 1-benzopyrano[3,4-c]pyrrolidines in good yields as a result of a 1,3-dipolar cycloaddition of the intermediate nonstabilized azomethine ylide at the Δ3-bond of the chromene system. © 2013 Elsevier Ltd. All rights reserved.

Subjects

Subjects :
3-NITRO-2H-CHROMENES
2 METHYL 8 METHOXY 3A NITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE
Azomethine ylide
2 METHYL 8 METHOXY 3A NITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE
UNCLASSIFIED DRUG
2 METHYL 8 METHOXY 3A NITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE
Biochemistry
Medicinal chemistry
8 BROMO 2 METHYL 3A NITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE
chemistry.chemical_compound
Drug Discovery
2 METHYL 3A NITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE
6A NITRO 6 (TRIFLUOROMETHYL) 6,6A,6B,7,8,9,11,11A OCTAHYDROCHROMENO[3,4 A]PYRROLIZINE
PRIORITY JOURNAL
Paraformaldehyde
STEREOCHEMISTRY
CHROMENE DERIVATIVE
2 METHYL 3A,8 DINITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE
2 METHYL 3A,8 DINITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE
Chemistry
2 BROMO 6A NITRO 6 (TRICHLOROMETHYL) 6,6A,6B,7,8,9,11,11A OCTAHYDROCHROMENO[3,4 A]PYRROLIZINE
2 BROMO 6A NITRO 6 (TRIFLUOROMETHYL) 6,6A,6B,7,8,9,11,11A OCTAHYDROCHROMENO[3,4 A]PYRROLIZINE
Cycloaddition
Drug synthesis
2 METHYL 3A,8 DINITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE
1,3-Dipolar cycloaddition
6A NITRO 6 PHENYL 6,6A,6B,7,8,9,11,11A OCTAHYDROCHROMENO[3,4 A]PYRROLIZINE
AZOMETHINE YLIDE
8 BROMO 2 METHYL 3A NITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE
CYCLOADDITION
Sarcosine
1-BENZOPYRANO[3,4-C]PYRROLIDINES
TRIFLUORO
2 METHYL 3A NITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE
METHYL 2 METHYL 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE 3A CARBOXYLATE
PYRROLIDINE DERIVATIVE
PARAFORMALDEHYDE
ARTICLE
2 METHYL 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE 3A CARBONITRILE
2 METHYL 8 METHOXY 3A NITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE
DRUG SYNTHESIS
Organic Chemistry
1,3-DIPOLAR CYCLOADDITION
CONTROLLED STUDY
NONSTABILIZED AZOMETHINE YLIDES
8 BROMO 2 METHYL 3A NITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE
Nitro
2 METHYL 3A NITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE
8 BROMO 2 METHYL 3A NITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE
2 METHYL 3A NITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE
2 METHYL 3A,8 DINITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE

Details

ISSN :
00404020
Volume :
69
Database :
OpenAIRE
Journal :
Tetrahedron
Accession number :
edsair.doi.dedup.....6141b2123cb4a88c867cadb36a4866f0
Full Text :
https://doi.org/10.1016/j.tet.2013.07.080
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